EP1929884A1 - Procédé de préparation des compositions de steroles - Google Patents

Procédé de préparation des compositions de steroles Download PDF

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Publication number
EP1929884A1
EP1929884A1 EP06025003A EP06025003A EP1929884A1 EP 1929884 A1 EP1929884 A1 EP 1929884A1 EP 06025003 A EP06025003 A EP 06025003A EP 06025003 A EP06025003 A EP 06025003A EP 1929884 A1 EP1929884 A1 EP 1929884A1
Authority
EP
European Patent Office
Prior art keywords
sterol
stanol
wet grinding
wettable
dispersion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06025003A
Other languages
German (de)
English (en)
Inventor
Peter Horlacher
Dieter Hietsch
Jörg SCHWARZER
Bernd Jenzer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP06025003A priority Critical patent/EP1929884A1/fr
Priority to JP2009539637A priority patent/JP5611595B2/ja
Priority to AU2007327973A priority patent/AU2007327973B2/en
Priority to EP07856258A priority patent/EP2099319A1/fr
Priority to US12/517,571 priority patent/US8414945B2/en
Priority to PCT/EP2007/010229 priority patent/WO2008067923A1/fr
Publication of EP1929884A1 publication Critical patent/EP1929884A1/fr
Priority to US13/790,547 priority patent/US20130216678A1/en
Priority to JP2013240706A priority patent/JP2014076054A/ja
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/20—Natural extracts
    • A23V2250/21—Plant extracts
    • A23V2250/2136—Phytosterols, phytostanols

Definitions

  • the invention is in the field of foodstuffs and relates to a process for the preparation of readily wettable phytosterol-containing formulations, the preparations prepared by this process and products, in particular foods, which contain these formulations.
  • the international registration WO 2005/074717 A1 uses a kind of protective colloid by embedding sterols in a matrix that contains proteins and carbohydrates.
  • the total content of sterols in the formulation is low due to the high proportion of excipients.
  • sterol-containing powder formulations The disadvantage of many sterol-containing powder formulations is the agglomeration behavior of the free sterols during storage. During storage, especially when stored under pressure, strong caking or clumping is observed, the solid, uncontrolled agglomerates must be crushed again in order to be processed.
  • agglomerates of sterol particles In the International Patent Application WO 2006/020980 A1 are described agglomerates of sterol particles.
  • the manufacturing method is an anodic granulation of an adhesive granulate in which the micronized sterol particles are wetted with a suspending agent in which a binder is partially or completely dissolved.
  • the suspending agent is removed after wetting, so that the remaining agglomerates have a size of 150 to 850 microns.
  • This process requires a high expenditure on equipment and must be controlled very precisely so that the agglomerates produced have the desired stability.
  • the inventive method makes it possible to produce powder with free unesterified sterols and stanols, which allow easy further processing of the lipophilic drugs without much equipment and at room temperature in food, especially drinks.
  • the powder has a low tendency to agglomerate and thus good flow properties. It is characterized by a good homogeneity and can be further processed due to its improved wettability without great technical effort, with a homogeneous distribution in the final formulation is achieved quickly.
  • the coating of the sterol surface with the hydrophilic additives decisively improves the organoleptic properties and the sensor technology.
  • the coated powder does not stick to teeth and oral mucosa, so that the unpleasant Stering taste, which leads to significant loss of taste in the active ingredient-containing foods is completely suppressed.
  • hydrophilic additives such as proteins, protein-containing auxiliaries, carbohydrates, sugar alcohols, fruit concentrates and vegetable concentrates not only improves solubilization properties and dispersing properties, but surprisingly, these powders also exhibit an increased storage stability compared to pure ground sterols, which have a high agglomeration tendency.
  • the process allows to dispense with the processing of unesterified sterols and stanols to organic solvents or heating of the formulation and despite the aqueous medium no emulsifiers with high surface activity specifically of the type of lecithins, monoglycerides, diglycerides, polysorbates, sodium stearyl lactylate, glycerol monostearate, lactic acid esters and Polyglycerolester use.
  • the low emulsifier properties of the hydrophilizing auxiliaries, in particular the caseinates, the milk powder or the gum arabic are sufficient to ensure the homogeneity of the powder produced and easy redispersibility and processability.
  • the elimination of further emulsifiers simplifies the further processing by reducing possible incompatibilities with other food ingredients and reduces the occurrence of incompatibilities with the consumer.
  • a particular advantage of the method is the implementation of milling and coating in one operation.
  • the application of the wet grinding method for comminuting the sterol particles avoids the high risk of powder explosions.
  • the particle size of the sterols and / or stanols used initially is relatively large, on the one hand to avoid powder explosions and on the other hand to ensure good handling. So can finished prills, the one have very high storage stability can be used.
  • the average particle sizes are over 1 mm. In this size, the particle size determination is carried out by a conventional sieve analysis.
  • the sterol and / or stanol particles in the final formulation after wet grinding are present in a particle size distribution with a D 90% of at most 50 ⁇ m, preferably a maximum of 40 ⁇ m and particularly preferably a maximum of 30 ⁇ m.
  • the particle size distribution was determined using a device from Beckman Coulter, type LS 230 and calculated as the volume distribution. The measurement was carried out in aqueous suspension.
  • the time required for grinding should be a maximum of 2 hours, preferably a maximum of 1 hour.
  • the mill to be used is based on a rotor-stator principle. Toothed colloid mills, but also Ultra-Turrax, corundum disc mills, perforated disc mills or annular gap ball mills, in which the balls are in the gap between the rotor and the housing, are suitable for the method according to the invention. Dental colloid mills have proved to be particularly advantageous. Based on the observation that the energy input during grinding must have a degree that on the one hand sufficient crushing without extreme heating of the ground material allows and on the other hand to lead to a low charge of the particles, these mills have proven particularly useful.
  • Shear forces exerted by high performance mills as seen in the European Patent EP 1148793 B1 are known for comminution of sterols, good storage stability without clumping of the particles, not beneficial. They have also been found to be detrimental to a uniform surface coating by the hydrophilizing additives.
  • the expenditure on equipment of the manufacturing apparatus according to the invention is thus very low. On a cooling of the ground material during milling can be dispensed with, the thermal load of the material is low. In addition, the risk of dust explosions is extremely reduced by the use of wet grinding.
  • the aqueous dispersions have concentrations of sterols and stanols of at least 20% by weight, preferably at least 30% by weight and more preferably at least 40% by weight and especially at least 50% by weight, based on the total weight of the dispersion.
  • these dispersions are dried.
  • the conventional drying methods such as vacuum drying or spray drying offer. Since the additives are used only for hydrophilization and the surface of the sterols coated with it the total content of sterols in the powders is very high.
  • the powder resulting after drying even contains at least 75% by weight, more preferably at least 85% by weight and in particular at least 90% by weight of sterols and / or stanols, based on the weight of the powder.
  • the sterol content of the final formulation depends on the amount of hydrophilic additive used.
  • the sterol-containing formulations prepared by these methods can be easily incorporated into foods, in particular milk, milk drinks, whey and yoghurt drinks, margarines, fruit juices, fruit juice mixtures, fruit juice drinks, vegetable juices, carbonated and non-carbonated beverages, soymilk beverages or high protein liquid diet replacement drinks, and fermented milk preparations.
  • Yogurt, drinking yoghurt, or cheese preparations but also be incorporated into pharmaceutical preparations.
  • the fruit or vegetable concentrate (also fruit or vegetable puree or fruit or vegetable pulp) can be previously dispersed in the suspension medium and thus diluted (step a)).
  • fruit or vegetable concentrate can be used directly as a suspending agent for the sterols and / or stanols, so that only the sterols and / or stanols are added to the concentrates and the resulting dispersion is comminuted and homogenized in the rotor-stator mill. Further additives listed in step a) are then not required.
  • the resulting formulations have a high content of sterols and / or stanols. As a rule, they have a yield point, ie they are solid, but they can be re-liquefied by shearing so that they can be further processed directly into final foodstuff formulations by simple means.
  • a further subject of the invention is therefore fruit and vegetable concentrates containing at least 1% by weight, preferably at least 5% by weight and more preferably at least 15% by weight of sterols and / or stanols, based on the concentrates.
  • These concentrates have a water content of at most 85% by weight, preferably at most 75% by weight and particularly preferably at most 65%, in order to have the consistency which is advantageous for further processing.
  • the sterol and / or stanol particles contained therein have a particle size distribution with a D 90% of not more than 50 ⁇ m, preferably not more than 40 ⁇ m and particularly preferably not more than 30 ⁇ m.
  • Another object of the invention relates to food preparations containing the sterol / stanol formulations of said composition. They are preferably used in beverages and milk products, which then contain 0.1 to 50 wt .-%, preferably 1 to 20 wt .-% of the powdered coated preparations based on the total weight of the food.
  • sterols derived from plants and vegetable raw materials so-called phytosterols and phytostanols are used.
  • Known examples are ergosterol, brassicasterol, campesterol, avenasterol, desmosterol, clionasterol, stigmasterol, poriferasterol, chalinosterol, sitosterol and mixtures thereof, among which ⁇ -sitosterol and campesterol are preferably used.
  • the hydrogenated saturated forms of the sterols, the so-called stanols are among the compounds used, and ⁇ -sitostanol and campestanol are also preferred here.
  • Soya beans, canola, palm kernels, corn, coconut, oilseed rape, cane, sunflower, olive, cotton, soy, peanut and tall oil products are among the sources of vegetable sources.
  • Milk powder and / or whey powder and / or casein and / or caseinates are preferably used as protein-containing auxiliaries and proteins.
  • Milk powder such as commercial whole milk and skimmed milk powder, which have been obtained from the respective milk qualities by drying, are particularly suitable. They can be used in mixtures with other proteins or as the sole carrier. If further proteins are added or proteins are used as a carrier instead of the milk powder, these are understood as meaning isolated proteins which are obtained from natural animal and vegetable sources and are added during the preparation of the pulverulent preparations.
  • Possible sources of proteins are plants such as wheat, soy, lupine, corn or sources of animal origin such as eggs or milk.
  • Skim milk powder is particularly preferred for the purposes of the present invention, since it has sufficient hydrophilizing properties without at the same time to show the disadvantages of such Anlagenemulgatoren described above, which are otherwise usually used especially for the production of beverages and dairy products, especially fermentation products such as yogurt.
  • skimmed milk powder best and best covers the typical unpleasant sterol taste Formulations with this additive have improved sensory properties over other excipients.
  • the compounds used as carbohydrates include all food-grade poly- and monosaccharides such as glucose, sucrose, fructose, trehalose, maltose, maltodextrin, cyclodextrin, invert sugar, palatinose, lactose, guar gum, xanthan, pectins, starch, starch derivatives and modified starch, alginates , Carrageenan, wheat gluten and gum arabic. Gum arabic, galactomannans such as guar gum, xanthan, starch and starch derivatives and modified starches (OSA starch) are preferably used as the carbohydrate, with gum arabic being particularly preferred.
  • the preparations according to the invention may contain antioxidants, preservatives and flow improvers.
  • antioxidants or preservatives are tocopherols, lecithins ascorbic acid, parabens, butylhydroxytoluene or -anisol, sorbic acid or benzoic acid and salts thereof.
  • Tocopherols are preferably used as antioxidants.
  • Silica can be used as the flow regulator and improver.
  • emulsifiers selected from the group consisting of lecithins, monoglycerides, diglycerides, polysorbates, sodium stearyl lactylate, glycerol monostearate, lactic acid esters and polyglycerol esters.
  • the powders thus obtained were dispersed in milk and water as compared to ground sterols of comparable particle size distribution.
  • about 250 ml of the zu placed in a beaker and stirred about 100 rpm.
  • To the stirred liquid was added 2.5 g of the respective powder and the dispersing behavior was evaluated.
  • the coated sterol was very well dispersed in cold (15 ° C) and warm (60 ° C) water and in milk (18 ° C), while the untreated sterol was poorly dispersed and remained on the liquid surface due to the hydrophobic surface.
  • the resulting powders are characterized by improved flowability, better stirrability in water and higher bulk density compared to conventional finely ground sterols.
  • the dried products have a sterol content of over 90%. In Example 1, the sterol content of the dried powder is 93%.
  • the powders can be introduced into aqueous systems such as water, juices, milk etc. simply by stirring them
  • the dispersions have a flow limit, are easy to stir and can easily be added to aqueous systems such as cold water, juices, milk, etc.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Botany (AREA)
  • Molecular Biology (AREA)
  • Mycology (AREA)
  • Medicinal Preparation (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Grain Derivatives (AREA)
EP06025003A 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles Withdrawn EP1929884A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP06025003A EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles
JP2009539637A JP5611595B2 (ja) 2006-12-04 2007-11-24 ステロール処方物の製造方法
AU2007327973A AU2007327973B2 (en) 2006-12-04 2007-11-24 Method for producing sterol formulations
EP07856258A EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol
US12/517,571 US8414945B2 (en) 2006-12-04 2007-11-24 Method for producing sterol formulations
PCT/EP2007/010229 WO2008067923A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol
US13/790,547 US20130216678A1 (en) 2006-12-04 2013-03-08 Method For Producing Sterol Formulations
JP2013240706A JP2014076054A (ja) 2006-12-04 2013-11-21 ステロール処方物の製造方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP06025003A EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles

Publications (1)

Publication Number Publication Date
EP1929884A1 true EP1929884A1 (fr) 2008-06-11

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP06025003A Withdrawn EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles
EP07856258A Withdrawn EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP07856258A Withdrawn EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol

Country Status (5)

Country Link
US (2) US8414945B2 (fr)
EP (2) EP1929884A1 (fr)
JP (2) JP5611595B2 (fr)
AU (1) AU2007327973B2 (fr)
WO (1) WO2008067923A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018132419A1 (fr) * 2017-01-11 2018-07-19 Empire Technology Development Llc Produits à base de résidus de déchets de noix de coco imprégnés de tréhalose
US11191289B2 (en) 2018-04-30 2021-12-07 Kraft Foods Group Brands Llc Spoonable smoothie and methods of production thereof
JP2020058287A (ja) * 2018-10-10 2020-04-16 ヤンマー株式会社 米ゲル製造システム及び米ゲル製造方法
CN115969036B (zh) * 2023-01-10 2024-05-07 丰益油脂科技有限公司 植物甾醇颗粒物及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000045648A1 (fr) * 1999-02-03 2000-08-10 Forbes Medi-Tech Inc. Procede de preparation de microparticules constituees de phytosterols ou de phytostanols
JP2004075541A (ja) * 2002-08-09 2004-03-11 Nof Corp ステロール類含有粉末組成物、圧縮成形物、製造方法及び用途
WO2005049037A1 (fr) * 2003-10-24 2005-06-02 The Coca-Cola Company Procede de preparation de dispersions de phytorosterol pour utilisation dans des boissons
WO2006020980A1 (fr) * 2004-08-13 2006-02-23 Cargill Incorporated Agglomeration de particules de sterol de taille particuliere

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3881005A (en) * 1973-08-13 1975-04-29 Lilly Co Eli Pharmaceutical dispersible powder of sitosterols and a method for the preparation thereof
FI105887B (fi) * 1996-09-27 2000-10-31 Suomen Sokeri Oy Elintarvike- ja terapeuttisiin sovelluksiin käyttökelpoiset, kasvisterolia sisältävät tuotteet, menetelmä niiden valmistamiseksi ja niiden käyttö
FI108110B (fi) * 1997-06-13 2001-11-30 Danisco Finland Oy Elintarvike- ja eläinravitsemusalalla käyttökelpoinen esiseos, menetelmä sen valmistamiseksi ja sen käyttö
US6423363B1 (en) 1997-08-22 2002-07-23 Lipton, Division Of Conopco, Inc. Aqueous dispersion
NZ508645A (en) 1998-06-05 2003-10-31 Forbes Medi Tech Inc Compositions comprising phytosterol and/or phytostanol having enhanced solubility and dispersability and the use of these compositions to lower serum cholesterol
US6113972A (en) * 1998-12-03 2000-09-05 Monsanto Co. Phytosterol protein complex
US6391370B1 (en) * 1999-11-12 2002-05-21 Kraft Foods, Inc. Micromilling plant sterols and emulsifiers
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
US20030165572A1 (en) * 2000-09-01 2003-09-04 Nicolas Auriou Water-dispersible encapsulated sterols
US20040047965A1 (en) * 2001-03-05 2004-03-11 Rudolf Haindl Milk product and process for its prouduction
AU2003230878A1 (en) 2002-04-10 2003-10-27 Cargill, Incorporated Aqueous dispersible steryl ester compositions
US7306819B2 (en) * 2002-06-12 2007-12-11 The Coca-Cola Company Beverages containing plant sterols
SI1549159T1 (sl) 2002-06-12 2009-04-30 Coca Cola Co Napitki, ki vsebujejo rastlinske sterole
DE10253111A1 (de) 2002-11-13 2004-05-27 Basf Ag Pulverförmige Phytosterol-Formulierungen
WO2005074717A1 (fr) 2004-01-30 2005-08-18 Unilever N.V. Matiere particulaire comportant des phytosterols et des compositions alimentaires comprenant une telle matiere cremeuse
US20050175672A1 (en) * 2004-02-10 2005-08-11 Kluetz Michael D. Particulate plant sterol compositions
US8968768B2 (en) * 2004-03-29 2015-03-03 Wyeth Llc Phytosterol nutritional supplements
KR20070086083A (ko) * 2004-11-17 2007-08-27 산에이겐 에후.에후. 아이. 가부시키가이샤 식물 스테롤류 함유 조성물 및 그의 제조방법
WO2006062699A2 (fr) * 2004-12-08 2006-06-15 William Conrad Franke Compositions et procedes d'apport de phytosterols hydrodispersables consommables
US8309156B2 (en) * 2005-12-20 2012-11-13 Pharmachem Laboratories, Inc. Compositions comprising one or more phytosterols and/or phytostanols, or derivatives thereof, and high HLB emulsifiers
JP2009519721A (ja) * 2005-12-20 2009-05-21 フォーブス メディ−テック インコーポレーテッド １種又はそれ以上のフィトステロール及び／又はフィトスタノール、又はその誘導体、及び高ｈｌｂ乳化剤を含む組成物。
US20110223312A1 (en) * 2009-11-30 2011-09-15 Daniel Perlman Triglyceride-encapsulated phytosterol microparticles dispersed in beverages

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000045648A1 (fr) * 1999-02-03 2000-08-10 Forbes Medi-Tech Inc. Procede de preparation de microparticules constituees de phytosterols ou de phytostanols
JP2004075541A (ja) * 2002-08-09 2004-03-11 Nof Corp ステロール類含有粉末組成物、圧縮成形物、製造方法及び用途
WO2005049037A1 (fr) * 2003-10-24 2005-06-02 The Coca-Cola Company Procede de preparation de dispersions de phytorosterol pour utilisation dans des boissons
WO2006020980A1 (fr) * 2004-08-13 2006-02-23 Cargill Incorporated Agglomeration de particules de sterol de taille particuliere

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200424, Derwent World Patents Index; AN 2004-252193, XP002437183 *

Also Published As

Publication number Publication date
JP5611595B2 (ja) 2014-10-22
AU2007327973A1 (en) 2008-06-12
JP2010511391A (ja) 2010-04-15
AU2007327973B2 (en) 2013-05-23
US8414945B2 (en) 2013-04-09
US20130216678A1 (en) 2013-08-22
WO2008067923A1 (fr) 2008-06-12
JP2014076054A (ja) 2014-05-01
US20100068367A1 (en) 2010-03-18
EP2099319A1 (fr) 2009-09-16

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